Synthesis of Enantiomerically Pure 2,2,3,4,5-Pentasubstituted Pyrrolidines by Phenylsulfanyl Migration

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4381-4384

  Baldwin, I Craig ^a   Briner, Paul ^a   Eastgate, Martin D ^b   Fox, David J ^b   Warren, Stuart ^b  

^a OSI Pharmaceuticals   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

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ARTICLE;

EID: 0442268854     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0268384     Document Type: Article

References (16)

1. Fox, D. J.; House, D.; Warren, S. Angew Chem., Int. Ed. 2002, 41, 2462 and references contained therein.
2. Aggarwal, V. K.; Eames, J.; Villa, M.-J.: McIntre, S.; Sansbury, F. H.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2000, 533.
3. Coldham, I.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 1637.
4. Caggiano, L.; Fox, D. J.; Warren, S. Chem. Commun. 2002, 2528.
5. Davies, S.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183.
6. Asao, N.; Uyehara, T.; Yamamoto, Y. Tetrahedron 1990, 46, 4563.
7. Davies, S.; Fenwick, D. J. Chem. Soc., Chem. Commun. 1997, 565.
8. Aggarwal, V. K.; Coldham, I.; McIntyre, S.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1991, 451.
9. Zimmerman, H.; Traxler, M. J. Am. Chem. Soc. 1957, 79, 1920.
10. 10b
11. (b) Sheldrick, G. M. SHELXS-97/SHELXL-97. University of Göttingen: Göttingen, Germany, 1997.
12. Sandrine, L.; Savigac, M.; Genet, D. Tetrahedron Lett. 1995, 1267.
13. Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S.; Smith, A. D. Chem. Commun. 2000, 337.
14. Typical procedure: to an acetonitrile (10 mL) solution of the amino alcohol (1 mmol) were added CDI (1.1 mmol) and DMAP (cat.). The reaction was heated at reflux until TLC analysis (4:1 hexane/EtOAc) indicated complete reaction. The solution was then concentrated onto silica and chromatographed, eluting 5-10% EtOAc in hexane, to yield the pyrrolidine as a clear colorless oil. NMR, HRMS, IR, and elemental analysis confirmed the structures of novel compounds.
15. Aggarwal, V. K.; Coldham, I.; McIntyre, S.; Sansbury, F. H.; Villa, M. J.; Warren, S. Tetrahedron Lett. 1988, 29, 4885.
16. 10b